Total Synthesis of the Post‐translationally Modified Polyazole Peptide Antibiotic Goadsporin

Dexter, Hannah L.; Williams, Huw E.L.; Lewis, William; Moody, Christopher J.

Abstract

The structurally unique polyazole antibiotic goadsporin contains six heteroaromatic oxazole and thiazole rings integrated into a linear array of amino acids that also contains two dehydroalanine residues. An efficient total synthesis of goadsporin is reported in which the key steps are the use of rhodium(II)-catalyzed reactions of diazocarbonyl compounds to generate the four oxazole rings, which demonstrates the power of rhodium carbene chemistry in organic chemical synthesis.

Citation

Dexter, H. L., Williams, H. E., Lewis, W., & Moody, C. J. (2017). Total Synthesis of the Post‐translationally Modified Polyazole Peptide Antibiotic Goadsporin. Angewandte Chemie International Edition, 56(11), 3069-3073. https://doi.org/10.1002/anie.201612103

• Journal Article Type: Article
• Acceptance Date: Feb 1, 2017
• Online Publication Date: Feb 1, 2017
• Publication Date: Mar 6, 2017
• Deposit Date: Sep 27, 2017
• Publicly Available Date: Sep 27, 2017
• Journal: Angewandte Chemie International Edition
• Print ISSN: 1433-7851
• Electronic ISSN: 1521-3773
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 56
• Issue: 11
• Pages: 3069-3073
• DOI: https://doi.org/10.1002/anie.201612103
• Keywords: antibiotics; diazo compounds; heterocycles; peptides; total synthesis
• Public URL: https://nottingham-repository.worktribe.com/output/849001
• Publisher URL: https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201612103
• Additional Information: This is the peer reviewed version of the following article: H. L. Dexter, H. E. L. Williams, W. Lewis, C. J. Moody, Angew. Chem. Int. Ed. 2017, 56, 3069, which has been published in final form at http://dx.doi.org/10.1002/anie.201612103. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
• Contract Date: Sep 27, 2017